US2010168093A1PendingUtilityA1
Substituted 3-amino-4 -hydroxy pyrrolidines compounds, their preparation and use as medicaments
Assignee: PERICAS-BRONDO MIGUEL ANGELPriority: Apr 28, 2006Filed: Apr 30, 2007Published: Jul 1, 2010
Est. expiryApr 28, 2026(expired)· nominal 20-yr term from priority
Inventors:Miguel Angel Pericas-BrondoAntoni Torrens-JoverSusana Yenes-MinguezFelix Cuevas CordobesCarmen Garcia Granda
C07D 401/04C07D 207/48A61P 25/28C07D 413/14C07D 207/14C07D 401/12C07D 471/04A61K 31/40
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Claims
Abstract
The present invention relates to substituted pyrrolidine compounds of general formula (I), methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animal.
Claims
exact text as granted — not AI-modified1 . Substituted pyrrolidine compounds of general formula (I),
wherein
R 1 represents a hydrogen atom, an unbranched or branched, saturated, optionally at least mono-substituted C 1-6 -aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; an optionally at least mono-substituted benzhydryl group; a (C═O)—R 5 group; a group; a (SO 2 )—R 6 group; or a (C═O)—NR 7 R 7a group;
R 2 represents a hydrogen atom; a substituted or unsubstituted aliphatic group; a (C═O)—R 8 group; a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH;
R 3 and R 4 , equal or different, represent a hydrogen atom; an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; with the condition (proviso) that R 3 and R 4 may not at the same time represent a hydrogen atom;
or
R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N 1 S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
R 5 and R 6 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 7 and R 7a , identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 8 represents a hydrogen atom; a branched or unbranched, saturated or unsaturated, unsubstituted aliphatic group;
R 9 , R 10 and R 11 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 12 and R 12a , identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
with the provisos that
if R 2 represents a hydrogen atom;
and R 1 represents a hydrogen atom or a condensed aryl group;
R 3 and R 4 may not form together with their bridging nitrogen atom a triazole group;
if R 2 represents a hydrogen atom;
and R 1 represents a hydrogen atom; a substituted C 1-2 alkyl group; a condensed aryl group; a benzyl group;
R 3 and R 4 may not form together with their bridging nitrogen atom a substituted, unsaturated, condensed ring system containing at least 4 nitrogen atoms as ring members; an unsaturated, (C═O)-substituted, uncondensed, 6-membered ring system in which one additional carbon atom is replaced by nitrogen.
if R 2 represents a hydrogen atom;
and R 3 and R 4 form together with their bridging nitrogen atom a pyrrolidine ring, a piperidine ring, a piperazine ring or a morpholine ring;
R 1 may not represent a hydrogen atom; a methyl group; an unsaturated tert-butyl group; a (C═O)-substituted alkyl-heteroaryl group;
if R 2 represents a hydrogen atom;
and R 1 does not represent a benzyl group;
and either R 3 or R 4 represents a hydrogen atom;
either R 3 or R 4 may not represent a substituted alkyl-heteroaryl group; an alkyl-aryl group; a substituted heteroaryl group; an unsubstituted methyl group; a substituted alkyl group; an aryl group; a cyclohexyl group; an alkyl-cycloalkyl group wherein the cycloalkyl group contains at least one heteroatom;
if R 2 represents a hydrogen atom;
and R 1 represents an alkyl group;
and either R 3 or R 4 represents a hydrogen atom; the other of R 3 or R 4 may not represent a substituted or unsubstituted C 1-2 alkyl group; a branched C 1-4 alkyl group; a substituted or unsubstituted C 3-6 cycloalkyl group in which optionally at least one carbon atom is optionally replaced by N, S or O; a cycloheptyl group;
if R 2 represents a hydrogen atom;
and R 1 represents an alkyl group;
either R 3 or R 4 may not represent a cyclohexyl group while the other represents at the same time an alkyl-aryl group; or either R 3 or R 4 may not represent an alkyl group while the other represents at the same time an alkyl-aryl group;
if R 2 represents a hydrogen atom;
and R 1 represents a benzhydryl group;
and either R 3 or R 4 represents a hydrogen atom;
either R 3 or R 4 may not represent a (C═O)-substituted alkyl-aryl group; a (C═O)-substituted aryl group;
if R 2 represents a hydrogen atom;
and R 1 represents benzyl;
and either R 3 or R 4 represents a hydrogen atom;
the other of R 3 or R 4 may not represent a substituted or unsubstituted C 1-2 alkyl group; an unsubstituted benzyl group; a C 3-8 substituted alkyl group; a substituted alkyl-aryl group;
or
R 3 or R 4 , together with their bridging nitrogen atom may not form a tetrahydropyrimidine ring; a triazolo pyrimidine ring;
if R 2 represents a benzyl group;
and either R 3 or R 4 represents a hydrogen atom either R 3 or R 4 may not represent a (C═O)-substituted alkyl-aryl group;
if R 2 represents a C 1-3 alkyl group;
and either R 3 or R 4 represents a hydrogen atom either R 3 or R 4 may not represent an unsubstituted C 1-2 alkyl group;
a substituted alkyl group; a substituted or unsubstituted aryl group; a substituted heteroaryl group; a (C═O)-substituted alkyl-aryl group;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
2 . Compound according to claim 1 , characterized in that R 1 represents a hydrogen atom, an unbranched or branched, optionally at least mono-substituted C 1-6 -alkyl radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; an optionally at least mono-substituted benzhydryl group; a (C═O)—R 5 group; a group; a (SO 2 )—R 8 group; or a (C═O)—NR 7 R 7a group;
R 2 represents a (C═O)—R 8 group, with R 8 representing a hydrogen atom; a branched or unbranched, saturated or unsaturated, unsubstituted aliphatic group; R 3 and R 4 , equal or different, represent a hydrogen atom; an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted C 1-8 -aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; with the condition (proviso) that R 3 and R 4 may not at the same time represent a hydrogen atom; or R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 2 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N 1 S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—N R 12 R 12a group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 11 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
R 5 , R 6 , R 7a , R 9 , R 10 , R 11 , R 12 and R 12a have the meaning according to claim 1 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
3 . Compounds according to claim 1 , characterized in that R 1 represents a hydrogen atom, an unbranched or branched, saturated, optionally at least mono-substituted C 1-6 -alkyl radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; an optionally at least mono-substituted benzhydryl group; a (C═O)—R 5 group; a group; a (SO 2 )—R 6 group; or a (C═O)—NR 7 R 7a group;
R 2 represents a linear, substituted or unsubstituted C C 1-6 alkyl group; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH; R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a — (C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
R 5 , R 6 , R 7 , R 7a , R 9 , R 10 , R 11 , R 12 and R 12a have the meaning according to claim 1 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
4 . Compounds according to claim 1 , characterized in that R 1 represents a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted heteroaryl group; a branched or unbranched, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; an optionally at least mono-substituted benzhydryl group; a (C═O)—R 5 group; a group; a (SO 2 )—R 6 group; or a (C═O)—NR 7 R 7a group;
R 2 represents a linear, substituted or unsubstituted C 1-6 alkyl group; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH; R 3 and R 4 , identical or different, represent a hydrogen atom; a saturated or unsaturated, unsubstituted C 3-8 aliphatic group; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group; an unsubstituted heteroaryl group; a saturated or unsaturated, optionally at least mono-substituted alkyl-cycloalkyl group; an unsubstituted alkyl-aryl group; a saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group; with the condition that R 3 and R 4 may not at the same time represent a hydrogen atom; R 5 , R 6 , R 7 and R 7a have the meaning according to claim 1 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
5 . Compounds according to claim 1 , characterized in that R 1 represents an unbranched or branched, optionally at least mono-substituted C 2-6 -alkyl radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated unsubstituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; an optionally at least mono-substituted benzhydryl group; a (C═O)—R 5 group; a (SO 2 )—R 6 group; a (C═O)—NR 7 R 7a group;
R 2 represents a hydrogen atom; R 3 and R 4 together with their bridging nitrogen atom form
1) a ring system A in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
2) an A-X—B group,
wherein
A represents a ring system in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 2 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 2 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
3) an A-X—B—Y—C group,
wherein
A represents a ring system in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 2 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
R 5 , R 6 , R 7 , R 7a , R 9 , R 10 , R 11 , R 12 and R 12a have the meaning according to claim 1 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
6 . Compounds according to claim 1 , characterized in that R 1 represents a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; an optionally at least mono-substituted benzhydryl group; a (C═O)—R 5 group; a (SO 2 )—R 6 group; or a (C═O)—NR 7 R 7a group;
R 2 represents a hydrogen atom; R 3 represents a hydrogen atom; R 4 represents a saturated or unsaturated, unsubstituted, linear C 3-8 aliphatic group; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing 4 or 5-membered cycloalkyl group; an unsubstituted heteroaryl group; a saturated or unsaturated, unsubstituted alkyl-cycloalkyl group; an unsubstituted C 1-6 alkyl-heteroaryl group; R 5 , R 6 , R 7 and R 7a have the meaning according to claim 1 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
7 . Compounds according to claim 1 , characterized in that R 1 represents a hydrogen atom, an unbranched or branched, saturated C 1-6 alkyl radical which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an optionally at least one heteroatom as ring member containing C 1-6 -alkyl-cycloalkyl group wherein the C 1-6 -alkyl and/or the cycloalkyl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an aryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 3-6 -alkyl-aryl group wherein the C 3-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 3-6 -alkyl-heteroaryl group wherein the C 3-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (C═O)—R 5 group; a (SO 2 )—R 6 group; or a (C═O)— NR 7 R 7a group;
R 2 represents a (C═O)—R 8 group, with R 8 representing a hydrogen atom; a branched or unbranched, saturated or unsaturated, unsubstituted aliphatic group; R 3 and R 4 , equal or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted C 1-8 -aliphatic radical; a saturated or unsaturated, optionally at least mono- substituted, optionally at least one heteroatom as ring member containing cycloalkyl group; a branched or unbranched, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing C 1-6 -alkyl-cycloalkyl group; an optionally at least mono-substituted aryl group; an optionally at least mono-substituted heteroaryl group; a branched or unbranched, optionally at least mono-substituted C 1-6 -alkyl-aryl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted C 1-6 -alkyl-heteroaryl group; with the condition that R 3 and R 4 may at the same time not represent a hydrogen atom; or R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 2 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 2 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 -(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
R 5 , R 6 , R 7 , R 7a , R 9 , R 10 , R 11 , R 12 and R 12a have the meaning according to claim 1 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
8 . Compounds according to claim 1 , characterized in that R 1 represents a hydrogen atom, an unbranched or branched, saturated C 1-6 alkyl radical which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , carboxy, amido, cyano, carbamyl, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an optionally at least one heteroatom as ring member containing C 1-6 -alkyl-cycloalkyl group wherein the C 1-6 -alkyl and/or the cycloalkyl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an aryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 2 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 1-6 -alkyl-aryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 2 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated, C 1-6 -alkyl-heteroaryl group wherein the C 1-6 -alkyl and/or the heteroaryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH 1 OH, SO 2 , CF 2 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an optionally at least mono-substituted benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 2 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (C═O)—R 5 group; a group; a (SO 2 )—R 6 group; or a (C═O)—NR 7 R 7a group;
R 2 represents a C 1-6 alkyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 2 ; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 2 ; R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 -(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
R 5 , R 6 , R 7 , R 7a , R 9 , R 10 , R 11 , R 12 and R 12a have the meaning according to claim 1 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
9 . Compounds according to claim 1 , characterized in that R 1 represents an optionally at least one heteroatom as ring member containing C 1-6 -alkyl-cycloalkyl group wherein the C 1-6 -alkyl and/or the cycloalkyl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 1-6 -alkyl-aryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 1-6 -alkyl-heteroaryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (C═O)—R 5 group; a (SO 2 )—R 6 group; or a (C═O)—NR 7 R 7a group;
R 2 represents a C 1-6 alkyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH 1 CF 3 ; R 3 and R 4 , identical or different, represent a hydrogen atom; a saturated or unsaturated, unsubstituted C 3-8 aliphatic group; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group with substituents independently selected from the group consisting of F 1 Cl, Br, I, NH 2 , SH, OH, CF 3 , CN 1 nitro; an unsubstituted heteroaryl group; an optionally at least mono-substituted C 1-6 alkyl-cycloalkyl group; an unsubstituted C 1-6 alkyl-aryl group; an unsubstituted C 1-6 alkyl-heteroaryl group; with the condition that R 3 and R 4 may not at the same time represent a hydrogen atom; R 5 , R 6 , R 7 and R 7a have the meaning according to claim 1 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
10 . Compounds according to claim 1 , characterized in that R 1 represents an unbranched or branched, optionally at least mono-substituted C 1-6 -alkyl radical which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an optionally at least one heteroatom as ring member containing C 1-6 -alkyl-cycloalkyl group wherein the C 1-6 -alkyl and/or the cycloalkyl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an aryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 3-6 -alkyl-aryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6 -alkyl-heteroaryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (C═O)—R 5 group; a (SO 2 )—R 6 group; or a (C═O)—NR 7 R 7a group;
R 2 represents a hydrogen atom; R 3 and R 4 together with their bridging nitrogen atom form
1) a 4 to 18 membered ring system A in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
2) an A-X—B group,
wherein
A represents 4 to 18 membered ring system in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12 group;
3) an A-X—B—Y—C group,
wherein
A represents 4 to 18 membered ring system in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 2 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a —O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
R 5 , R 5 , R 7 , R 7a , R 9 , R 10 , R 11 , R 12 and R 12a have the meaning according to claim 1 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
11 . Compounds according to any of claims 1 , characterized in that R 1 represents an optionally at least one heteroatom as ring member containing cycloalkyl group wherein the C 1-6 -alkyl and/or the cycloalkyl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6 -alkyl-aryl group wherein the C 1-6 -alkyl and/or the aryl group is optional: substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6 -alkyl-heteroaryl group wherein the C 1-6 -alkyl and/or the aryl group is optional: substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN 1 nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (C═O)—R 5 group; a (SO 2 )—R 6 group; or a (C═O)—NR 7 R 7a group;
R 2 represents a hydrogen atom; R 3 represents a hydrogen atom; R 4 represents a saturated or unsaturated, unsubstituted, linear C 3-8 aliphatic group; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing 4 or 5-membered cycloalkyl group; an unsubstituted heteroaryl group; a saturated or unsaturated, unsubstituted alkyl-cycloalkyl group; an unsubstituted C 1-6 alkyl-heteroaryl group; R 5 , R 6 , R 7 and R 7a have the meaning according to claim 1 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
12 . Compound according to claim 1 , characterized in that R 1 represents a hydrogen atom, an unbranched or branched C 1-6 alkyl radical which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH; OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an optionally at least one heteroatom as ring member containing C 1-6 -alkyl-cycloalkyl group wherein the C 1-6 -alkyl and/or the cycloalkyl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an aryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN 1 nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6 -alkyl-aryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6 -alkyl-heteroaryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN 1 nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (SO 2 )—R 6 group;
R 2 represents a (C═O)—R 8 group, with R 8 representing a hydrogen atom; a methyl group; an ethyl group; a propyl group; a butyl group; a pentyl group; a hexyl group; R 3 and R 4 , equal or different, represent a hydrogen atom, an unbranched or branched C 1-8 -alkyl group, which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a saturated or unsaturated, optionally at least one heteroatom as ring member containing cycloalkyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, optionally at least one heteroatom as ring member containing C 1-6 -alkyl-cycloalkyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an aryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, CO—OH, CO—O—CH 3 , O—CH 3 , nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, CO—OH, CO—O—CH 3 , O—CH 3 , nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6 -alkyl-aryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, CO—OH, CO—O—CH 3 , O—CH 3 , nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6 -alkyl-heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; with the condition that R 3 and R 4 may at the same time not represent a hydrogen atom; or R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated 4 to 18 membered ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a OH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated 4 to 18 membered ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted 0 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group;
a NH—R 11 group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated 4 to 18 membered ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11n group; a NH—R 11 group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 -(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH 1 OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 -(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
R 6 represents a hydrogen atom; a C 1-6 alkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , or CN; an alkyl-cycloalkyl group which is optionally at least mono- substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a branched or unbranched alkyl-aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; R 9 , R 10 and R 11 represent a hydrogen atom, an unbranched or branched C 1-6 alkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-cycloalkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a branched or unbranched alkyl-aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
13 . Compounds according to claim 1 , characterized in that R 1 represents a hydrogen atom, an unbranched or branched C 1-6 alkyl radical which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , carboxy, amido, cyano, carbamyl, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an optionally at least one heteroatom as ring member containing C 1-6 -alkyl-cycloalkyl group wherein the C 1-6 -alkyl and/or the cycloalkyl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an aryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 1-6 -alkyl-aryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated, C 16 -alkyl-heteroaryl group wherein the C 1-6 -alkyl and/or the heteroaryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an optionally at least mono-substituted benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a group; a (SO 2 )—R 6 group;
R 2 represents a methyl , ethyl, propyl or butyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated 4 to 18 membered ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 3-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 -(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated 4 to 18 membered ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated 4 to 18 membered ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
R 6 represents a hydrogen atom; a C 1-6 alkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , or CN; an alkyl-cycloalkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a branched or unbranched alkyl-aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; R 9 , R 10 and R 11 represent a hydrogen atom, an unbranched or branched C 1-6 alkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-cycloalkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a branched or unbranched alkyl-aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
14 . Compounds according to claim 1 , characterized in that re represents an optionally at least one heteroatom as ring member containing C 1-6 -alkyl-cycloalkyl group wherein the C 1-6 -alkyl and/or the cycloalkyl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 1-6 -alkyl-aryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 1-6 -alkyl-heteroaryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I 1 NH 2 , SH 1 OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (SO 2 )—R 6 group;
R 2 represents a methyl, ethyl, propyl or butyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; R 3 and R 4 , identical or different, represent a hydrogen atom; a saturated or unsaturated, unsubstituted C 3-6 aliphatic group; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group with substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , CN, nitro; an unsubstituted heteroaryl group; a C 1-6 alkyl-cycloalkyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an unsubstituted C 1-6 alkyl-aryl group; an unsubstituted C 1 - 6 alkyl-heteroaryl group; with the condition that R 3 and R 4 may not at the same time represent a hydrogen atom; R 6 represents a hydrogen atom; a C 1-6 alkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , or CN; an alkyl-cycloalkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a branched or unbranched alkyl-aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
15 . Compounds according to claim 1 , characterized in that R 1 represents an unbranched or branched, saturated, optionally at least mono-substituted C 1-6 -alkyl radical which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an optionally at least one heteroatom as ring member containing C 1-6- alkyl-cycloalkyl group wherein the C 1-6- alkyl and/or the cycloalkyl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; an aryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 1-6- alkyl-heteroaryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (SO 2 )—R 6 group;
R 2 represents a hydrogen atom; R 3 and R 4 together with their bridging nitrogen atom form
1) a 4 to 18 membered ring system A in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
2) an A-X—B group,
wherein
A represents a 4 to 18 membered ring system in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
X group; a —NH— group; a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
3) an A-X—B—Y—C group,
wherein
A represents a 4 to 18 membered ring system in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH 2 —(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated 4 to β membered ring system, in which at least 1 carbon atom is optionally replaced by N or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, or CF 3 ;
R 6 represents a hydrogen atom; a C 1-6 alkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , or CN; an alkyl-cycloalkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a branched or unbranched alkyl-aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; R 9 , R 10 and R 11 represent a hydrogen atom, an unbranched or branched alkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-cycloalkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a branched or unbranched alkyl-aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
16 . Compounds according to claim 1 , characterized in that R 1 represents an optionally at least one heteroatom as ring member containing C 1-6- alkyl-cycloalkyl group wherein the C 1-6- alkyl and/or the cycloalkyl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN 1 nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a heteroaryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 1-6 -alkyl-aryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched, saturated C 1-6- alkyl-heteroaryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (SO 2 )—R 6 group;
R 2 represents a hydrogen atom; R 3 represents a hydrogen atom; R 4 represents a saturated or unsaturated, unsubstituted, linear C 3-13 aliphatic group; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing 4 or 5-membered cycloalkyl group; an unsubstituted heteroaryl group; a saturated or unsaturated, unsubstituted alkyl-cycloalkyl group; an unsubstituted C 1-6 alkyl-heteroaryl group; R 6 represents a hydrogen atom; a C 1-6 alkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a cycloalkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, pyrroline, pyrrolidine, pyrrolidineone, pyrazoline, pyrazolinone, oxopyrazolinone, aziridine, acetidine, tetrahydropyrrole, oxirane, oxetane, dioxetane, tetrahydrofurane, dioxane, dioxolane, oxathiolane, oxazolidine, thiirane, thietane, thiolane, thiane, thiazolidine, piperidine, piperazine or morpholine which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , or CN; an alkyl-cycloalkyl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a branched or unbranched alkyl-aryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; an alkyl-heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
17 . Compounds according to claim 1 , characterized in that R 1 represents a branched or unbranched C 1-6- alkyl-aryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6- alkyl-heteroaryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (SO 2 )—R 6 group with R 6 being an aryl group, preferably a phenyl or a naphtyl group, which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ;
R 2 represents a (C═O)—R 8 group, with R 8 representing a hydrogen atom; a methyl group; an ethyl group; a propyl group; a butyl group; a pentyl group; a hexyl group; R 3 and R 4 , identical or different, represent a hydrogen atom; a C 3-8 alkyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , CN; an optionally at least mono-substituted quinoline group; a phenyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , CN; a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , CN; with the condition that R 3 and R 4 may not at the same time represent a hydrogen atom; or R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated 4 to 18 membered ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated 4 to 18 membered ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R n being a linear or branched C 1-6 alkyl group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated 4 to 18 membered ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 2 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
18 . Compounds according to claim 1 , characterized in that R 1 represents a branched or unbranched C 1-6- alkyl-aryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6- alkyl-heteroaryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (SO 2 )—R 6 group with R 6 being an aryl group, preferably a phenyl or a naphtyl group, which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ;
R 2 represents a methyl, ethyl, propyl or butyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated 4 to 18 membered ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 16 group with R 10 being a linear or branched C 1-6 alkyl group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated 4 to 18 membered ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated 4 to 18 membered ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
19 . Compounds according to any of claim 1 , characterized in that R 1 represents a branched or unbranched C 1-6- alkyl-aryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6- alkyl-heteroaryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (SO 2 )—R 6 group with R 6 being an aryl group, preferably a phenyl or a naphtyl group, which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ;
R 2 represents a methyl, ethyl, propyl or butyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; R 3 and R 4 , identical or different, represent a hydrogen atom; a saturated or unsaturated, optionally at least mono-substituted C 3-8 aliphatic group with substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , CN, nitro; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group with substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , CN, nitro; an unsubstituted heteroaryl group; a saturated or unsaturated, optionally at least mono-substituted C 1-6 alkyl-cycloalkyl group; a saturated or unsaturated, unsubstituted C 1-6 alkyl-aryl group; a saturated or unsaturated, unsubstituted C 1-6 alkyl-heteroaryl group; with the condition that R 3 and R 4 may not at the same time represent a hydrogen atom; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
20 . Compounds according to claim 1 , characterized in that R 1 represents a branched or unbranched C 1-6- alkyl-aryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6- alkyl-heteroaryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (SO 2 )—R 6 group with R 6 being an aryl group, preferably a phenyl or a naphtyl group, which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ;
R 2 represents a hydrogen atom; R 3 and R 4 together with their bridging nitrogen atom form
1) a 4 to 18 membered ring system A in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
2) an A-X—B group,
wherein
A represents a 4 to 18 membered ring system in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
3) an A-X—B—Y—C group,
wherein
A represents a 4 to 18 membered ring system in which the ring containing the nitrogen atom is saturated, but may be condensed with an unsaturated ring, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated 4 to 12 membered ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
21 . Compounds according to claim 1 , characterized in that R 1 represents a branched or unbranched C 1-6- alkyl-aryl group wherein the C 1-6- alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a branched or unbranched C 1-6- alkyl-heteroaryl group wherein the C 1-6 -alkyl and/or the aryl group is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a benzhydryl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 3 , CN, nitro, —SO 2 NH 2 or C 1-6 -alkoxy; a (SO 2 )—R 6 group with R 6 being an aryl group, preferably a phenyl or a naphtyl group, which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a heteroaryl group which is optionally at least mono-substituted by substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ;
R 2 represents a hydrogen atom; R 3 represents a hydrogen atom; R 4 represents a saturated or unsaturated, unsubstituted, linear C 3-6 aliphatic group; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing 4 or 5-membered cycloalkyl group; an unsubstituted heteroaryl group; a saturated or unsaturated, unsubstituted alkyl-cycloalkyl group; an unsubstituted C 1-6 alkyl-heteroaryl group; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
22 . Compounds according to claim 1 , characterized in that R 1 represents a benzyl group or a (SO 2 )—R 6 group with R 6 being an aryl group;
R 2 represents a (C═O)—R 8 group, with R 8 representing a hydrogen atom; a methyl group; an ethyl group; a propyl group; a butyl group; a pentyl group; a hexyl group; R 3 and R 4 , identical or different, represent a C 3-8 alkyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , CN; an optionally at least mono-substituted quinoline group; a phenyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , CN; a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , CN; or R 3 and R 4 together with their bridging nitrogen atom form
1) a ring system A, comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
2) an A-X—B group,
wherein
A represents a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a linear optionally substituted C 1-2 alkyl chain, —O—, or a —SO 2 — group;
B represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
3) an A-X—B—Y—C group,
wherein
A represents a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a linear C 1-2 alkyl chain, —O—, or a —SO 2 — group;
B represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
Y represents a bond, a —NH— group, a linear C 1-2 -aliphatic group;
C represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
23 . Compounds according to claim 1 , characterized in that R 1 represents a benzyl group or a (SO 2 )—R 6 group with R 6 being an aryl group;
R 2 represents a methyl, ethyl, propyl or butyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; R 3 and R 4 together with their bridging nitrogen atom form
1) a ring system A, comprising:
and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
2) an A-X—B group,
wherein
A represents a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a linear C 1-2 alkyl chain, —O—, or a —SO 2 — group;
B represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
3) an A-X—B—Y—C group,
wherein
A represents a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a linear C 1-2 alkyl chain, —O—, or a —SO 2 — group;
B represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
Y represents a bond, a —NH— group, a linear C 1-2 alkyl group;
C represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
24 . Compounds according to claim 1 , characterized in that R 1 represents a benzyl group or a (SO 2 )—R 6 group with R 6 being an aryl group;
R 2 represents a hydrogen atom; R 3 and R 4 together with their bridging nitrogen atom form
1) a ring system A, comprising:
and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
2) an A-X—B group,
wherein
A represents a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a linear C 1-2 alkyl chain, —O—, or a —SO 2 — group;
B represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
3) an A-X—B—Y—C group,
wherein
A represents a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a linear C 1-2 alkyl chain, —O—, or a —SO 2 — group;
B represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 alkoxy group;
Y represents a bond, a —NH— group, a linear C 1-2 -alkyl group;
C represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
25 . Compounds according to claim 1 selected from the group consisting of
[1] (3,4-trans)-1-benzyl-4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrrolidine-3-ol, [2] (3,4-trans)-1-benzyl-4-morpholinopyrrolidine-3-ol, [3] (3,4-trans)-1-benzyl-4-(4-(2-methyl-3H-imidazo[4,5-b]pyridin-3-yl)piperidin-1-yl)pyrrolidine-3-ol, [4] (3,4-trans)-1-benzyl-4-(3-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)propyl amino)pyrrolidine-3-ol, [5] (3,4-trans)-1-benzyl-4-(4-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)piperidin-1-yl)pyrrolidine-3-ol, [6] 1-(4-(6-((3,4-trans)-1-benzyl-4-hydroxypyrrolidine-3-yl)-5,6,7,8-tetrahydropyrido [4,3-d]pyrimidin-2-ylamino)phenyl)ethanone, [7] 1-(1-((3,4-trans)-1-benzyl-4-hydroxypyrrolidine-3-yl)piperidin-4-yl)-1H-benzo[d] [1,3] oxazin-2(4H)-one, [8] (3,4-trans)-1-benzyl-4-(2-(4-phenoxyphenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)pyrrolidine-3-ol, [9] (3,4-trans)-1-benzyl-4-(3-(3,4-dihydroisoquinolin-2(1H)-yl)propylamino)pyrrolidine -3-ol, [10] (3,4-trans)-1-benzyl-4-(4-(4-methoxypyrimidin-2-yl)piperazin-1-yl)pyrrolidine-3-ol, [11] (3,4-trans)-1-benzyl-4-(2,3,8,8a-tetrahydrocyclopenta[ij]isoquinolin-1(7H)-yl)pyrrolidine-3-ol, [12] tert-butyl-4-((3,4-trans)-1-benzyl-4-hydroxypyrrolidine-3-yl)piperazine-1-carboxylate, [13] tert-butyl 4-((3,4-trans)-4-hydroxy-1-(phenylsulfonyl)pyrrolidine-3-yl)piperazine-1-carboxylate, [14] (3,4-trans)-4-morpholino-1-(phenylsulfonyl)pyrrolidine-3-ol, [15] (3,4-trans)-4-(3,4-dihydroisoquinolin-2(1H)-yl)-1-(phenylsulfonyl)pyrrolidine-3-ol, [16] (3,4-trans)-4-(3,4-dihydroisoquinolin-2(1H)-yl)-1((S)-I-phenylethyl)pyrrolidine-3-ol, [17] (3,4-trans)-1-benzyl-4-(4-benzylpiperazin-1-yl)pyrrolidine-3-ol, [18] (3,4-trans)-1-benzyl-4-(4-phenylpiperazin-1-yl)pyrrolidine-3-ol, [19] Ethyl 2-(4-((3,4-trans)-1-benzyl-4-hydroxypyrrolidine-3-yl)piperazin-1-yl)acetate, [20] (4-((3,4-trans)-1-benzyl-4-hydroxypyrrolidine-3-yl)piperazin-1-yl)(phenyl)methanone, [21] Ethyl 4-((3,4-trans)-1-benzyl-4-hydroxypyrrolidine-3-yl)piperazine-1-carboxilate, [22] tert-butyl 4-((3,4-trans)-1-(4-fluorobenzyl)-4-hydroxypyrrolidine-3-yl)piperazine-1-carboxylate, [23] (3,4-trans)-1-benzyl-4-(4-methylpiperazin-1-yl)pyrrolidine-3-ol, [24] tert-butyl-4-(3,4-trans)-4-acetoxy-1-benzylpyrrolidine-3-yl)piperazine-1-carboxylate, [25] (3,4-trans)-1-benzyl-4-(piperazin-1-yl)pyrrolidine-3-yl acetate, [26] tert-butyl 4-((3,4-trans)-4-acetoxypyrrolidine-3-yl)piperazine-1-carboxylate, [27] trans 1-Benzyl-4-(4-(2-phenyl-phenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate, [28] trans 1-Benzyl-4-(4-(2-phenyl-phenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [29] (3,4-trans)-1-benzyl-4-(phenylamino)pyrrolidin-3-ol, [30] (3,4-trans)-1-benzyl-4-(benzylamino)pyrrolidin-3-ol, [31] (3R,4R)-1-benzyl-4-(octylamino)pyrrolidin-3-ol, [32] (3,4-trans)-1-benzyl-4-(4-methoxybenzylamino)pyrrolidin-3-ol, [33] (3,4-trans)-1-benzyl-4-(butylamino)pyrrolidin-3-ol, [34] (3R,4R)-1-benzyl-4-(4-(4-chloro-2,5-dimethylphenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate, [35] (3R,4R)-1-benzyl-4-(4-tosylpiperazin-1-yl)pyrrolidin-3-yl acetate, [36] (3,4-trans)-1-benzyl-4-(butylamino)pyrrolidin-3-ol, [37] (3R,4R)-1-benzyl-4-(4-methoxyphenylamino)pyrrolidin-3-ol, [38] Methyl 4-((3,4-trans)-1-benzyl-4-hydroxypyrrolidin-3-ylamino)benzoate, [39] (3R,4R)-1-benzyl-4-(4-(naphthalen-1-ylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate, [40] (3R,4R)-1-benzyl-4-(4-(2-chlorophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol, [41] (3R,4R)-1-benzyl-4-(4-(2-bromophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate, [42] (3R,4R)-1-benzyl-4-(4-(2-bromophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol, [43] (3R,4R)-1-benzyl-4-(4-(5-fluoro-2-methylphenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate, [44] (3R,4R)-1-benzyl-4-(4-(5-fluoro-2-methylphenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol, [45] (3R,4R)-1-benzyl-4-(4-(phenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate, [46] (3R,4R)-1-benzyl-4-(4-(phenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol, [47] (3R,4R)-1-benzyl-4-(4-(2-fluorophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate, [48] (3R,4R)-1-benzyl-4-(4-(2-fluorophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol, [49] (3R,4R)-1-benzyl-4-(4-(naphthalen-1-ylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol, [50] (3R,4R)-1-benzyl-4-(4-(4-chloro-2,5-dimethylphenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol, [51] (3R,4R)-1-benzyl-4-(4-tosylpiperazin-1-yl)pyrrolidin-3-ol, [52] (3R,4R)-1-benzyl-4-(4-(2-chlorophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate, [53] (3,4-trans)-1-benzyl-4-(4-(4-chloro-2,5-dimethylphenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate dihydrochloride, [54] (3,4-trans)-1-benzyl-4-(4-(4-chloro-2,5-dimethylphenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [55] (3S,4S)-1-benzyl-4-(4-(4-chloro-2,5-dimethylphenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [56] (3,4-trans)-1-benzyl-4-(4-tosylpiperazin-1-yl)pyrrolidin-3-yl acetate dihydrochloride, [57] (3,4-trans)-1-benzyl-4-(4-tosylpiperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [58] (3R,4R)-1-benzyl-4-(4-tosylpiperazin-1-yl)pyrrolidin-3-ol dihydorchloride, [59] (3S,4S)-1-benzyl-4-(4-tosylpiperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [60] (3,4-trans)-1-benzyl-4-(4-(naphthalen-1-ylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate dihydrochloride, [61] (3,4-trans)-1-benzyl-4-(4-(naphthalen-1-ylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [62] (3S-4S)-1-benzyl-4-(4-(naphthalen-1-ylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [63] (3,4-trans)-1-benzyl-4-(4-(2-chlorophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate dihydrochloride, [64] (3,4-trans)-1-benzyl-4-(4-(2-chlorophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [65] (3S,4S)-1-benzyl-4-(4-(2-chlorophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [66] (3,4-trans)-1-benzyl-4-(4-(2-bromophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate dihydrochloride, [67] (3,4-trans)-1-benzyl-4-(4-(2-bromophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [68] (3S,4S)-1-benzyl-4-(4-(2-bromophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [69] (3,4-trans)-1-benzyl-4-(4-(5-fluoro-2-methylphenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate dihydrochloride, [70] (3,4-trans)-1-benzyl-4-(4-(5-fluoro-2-methylphenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [71] (3S,4S)-1-benzyl-4-(4-(5-fluoro-2-methylphenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [72] (3,4-trans)-1-benzyl-4-(4-(phenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate, [73] (3,4-trans)-1-benzyl-4-(4-(phenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol, [74] (3S,4S)-1-benzyl-4-(4-(phenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol, [75] (3,4-trans)-1-benzyl-4-(4-(2-fluorophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-yl acetate dihydrochloride, [76] (3,4-trans)-1-benzyl-4-(4-(2-fluorophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [77] (3S,4S)-1-benzyl-4-(4-(2-fluorophenylsulfonyl)piperazin-1-yl)pyrrolidin-3-ol dihydrochloride, [78] (3,4-trans)-1-benzyl-4-(4-(2-chloro-6-fluorobenzyl)piperazin-1-yl)pyrrolidine-3-ol [79] (3,4-trans)-1-benzyl-4-(4-(3,4-dichlorobenzyl)piperazin-1-yl)pyrrolidine-3-ol [80] (3,4-trans)-1-benzyl-4-hydroxypyrrolidin-3-yl)piperazin-1-yl)(furan-2-yl)methanone [81] (3,4-trans)-1-benzyl-4-(4-ethylpiperazin-1-yl)pyrrolidin-3-ol, [82] (3,4-trans)-1-benzyl-4-(4-(2-methoxyphenyl)piperazin-1-yl)pyrrolidin-3-ol, [83] (3,4-trans)-1-benzyl-4-(4-(4-fluorophenyl)piperazin-1-yl)pyrrolidin-3-ol, [84] (3,4-trans)-1-benzyl-4-(4-(2-chlorophenyl)piperazin-1-yl)pyrrolidin-3-ol, [85] (3R,4R)-1-benzyl-4-(4-(2-chlorophenyl)piperazin-1-yl)pyrrolidin-3-ol, [86] (35,45)-1-benzyl-4-(4-(2-chlorophenyl)piperazin-1-yl)pyrrolidin-3-ol, [87] 1-(4-((3,4-trans)-1-benzyl-4-hydroxypyrrolidin-3-yl)piperazin-1-yl)ethanone, [88] (3,4-trans)-1-benzyl-4-(4-(3,4-dichlorophenyl)piperazin-1-yl)pyrrolidin-3-ol, [89] (3,4-trans)-1-benzyl-4-(4-(3,4-dichlorophenyl)piperazin-1-yl)pyrrolidin-3-ol,
or
[90] (3,4-trans)-cert-butyl 3-(3,4-dihydroisoquinolin-2(1H)-yl)-4-hydroxypyrrolidine-1-carboxylate; optionally in form of a corresponding salt, or a corresponding solvate.
26 . Substituted pyrrolidine compounds according to claim 1 of general formula (IA),
wherein
Z represents H or CH 3 ;
R 2 represents a hydrogen atom; a substituted or unsubstituted aliphatic group; a (C═O)—R 8 group; a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH;
R 3 and R 4 , equal or different, represent a hydrogen atom; an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; with the condition (proviso) that R 3 and R 4 may not at the same time represent a hydrogen atom;
or
R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, N11 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 10 group; or a (C═O)—NR 12 R 12a group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)— O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
R 8 represents a hydrogen atom; a branched or unbranched, saturated or unsaturated, unsubstituted aliphatic group;
R 9 , R 10 and R 11 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 12 and R 12a , identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
W represents F, Cl, Br, I, NH 2 , SH, OH, SO 2 , CF 2 , carboxy, amido, cyano, carbamyl, nitro, phenyl, benzyl, —SO 2 NH 2 , C 1-6 alkyl and/or C 1-6 -alkoxy;
r represents either 0, 1, 2 or 3;
with the provisos that
if R 2 represents a hydrogen atom;
R 3 and R 4 may not form together with their bridging nitrogen atom a triazole group;
if R 2 represents a hydrogen atom;
R 3 and R 4 may not form together with their bridging nitrogen atom a substituted, unsaturated, condensed ring system containing at least 4 nitrogen atoms as ring members; an unsaturated, (C═O)-substituted, uncondensed, 6-membered ring system in which one additional carbon atom is replaced by nitrogen.
if R 2 represents a hydrogen atom;
and either R 3 or R 4 represents a hydrogen atom;
the other of R 3 or R 4 may not represent a substituted or unsubstituted C 1-2 alkyl group; an unsubstituted benzyl group; a C 3-8 substituted alkyl group; a substituted alkyl-aryl group;
or
R 3 or R 4 , together with their bridging nitrogen atom may not form a a tetrahydropyrimidine ring; a triazolo pyrimidine ring;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
27 . Substituted pyrrolidine compounds according to claim 26 wherein Z represents H or CH 3 ; preferably Z represents H; R 2 represents a hydrogen atom; a methyl, ethyl, propyl or butyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a (C═O)—R 8 group, with R 8 representing a hydrogen atom; a methyl group; an ethyl group; a propyl group; a butyl group; a pentyl group; a hexyl group; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; preferably R 2 represents a hydrogen atom; a (C═O)—R 8 group, with R 8 representing a hydrogen atom; a methyl group; an ethyl group; a propyl group; a butyl group; a pentyl group; a hexyl group R 3 and R 4 , identical or different, represent a hydrogen atom; a saturated or unsaturated, unsubstituted C 3-8 aliphatic group; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group; an unsubstituted heteroaryl group; a saturated or unsaturated, optionally at least mono-substituted alkyl-cycloalkyl group; an unsubstituted alkyl-aryl group; a saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group; with the condition that R 3 and R 4 may not at the same time represent a hydrogen atom; or R 3 and R 4 together with their bridging nitrogen atom form
1) a ring system A, comprising:
and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
2) an A-X—B group,
wherein
A represents a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a linear C 1-2 alkyl chain, —O—, or a —SO 2 — group;
B represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
3) an A-X—B—Y—C group,
wherein
A represents a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a linear C 1-2 alkyl chain, —O—, or a —SO 2 — group;
B represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 alkoxy group;
Y represents a bond, a —NH— group, a linear C 1-2 -alkyl group;
C represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
R 8 represents a hydrogen atom; a branched or unbranched, saturated or unsaturated, unsubstituted aliphatic group;
R 9 , R 10 and R 11 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 12 and R 12a , identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
W represents substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , OCF 3 , unsubstituted C 1-6 alkyl and/or unsubstituted C 1-6 -alkoxy;
r represents either 0, 1, 2 or 3;
with the provisos that
if R 2 represents a hydrogen atom;
R 3 and R 4 may not form together with their bridging nitrogen atom a triazole group; a substituted, unsaturated, condensed ring system containing at least 4 nitrogen atoms as ring members; an unsaturated, (C═O)— substituted, uncondensed, 6-membered ring system in which one additional carbon atom is replaced by nitrogen; or may not form a tetrahydropyrimidine ring; a triazolo pyrimidine ring
if R 2 represents a hydrogen atom;
and either R 3 or R 4 represents a hydrogen atom;
the other of R 3 or R 4 may not represent a substituted or unsubstituted C 1-2 alkyl group; an unsubstituted benzyl group; a C 3-8 substituted alkyl group; a substituted alkyl-aryl group;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
28 . Substituted pyrrolidine compounds according to claim 27 , according to either formula (IAa) or (IAb)
wherein
R 2 represents a hydrogen atom; a methyl, ethyl, propyl or butyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a (C═O)—R 8 group, with R 8 representing a hydrogen atom; a methyl group; an ethyl group; a propyl group; a butyl group; a pentyl group; a hexyl group; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; preferably R 2 represents hydrogen or (C═O)—CH 3 ;
R 4 ,—if present as in case of general formula (IAb)—represents a saturated or unsaturated, unsubstituted C 3-8 aliphatic group; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group; an unsubstituted heteroaryl group; a saturated or unsaturated, optionally at least mono-substituted alkyl-cycloalkyl group; an unsubstituted alkyl-aryl group; a saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group;
or
Q—if present as in case of general formula (IAa)—represents N or CH, preferably Q represents N; and
Rx—if present as in case of general formula (IAa)—represents
hydrogen; a —(C═O)R 8 group with R 8 being either hydrogen or an optionally substituted C 1-6 aliphatic group; or a —(C═O)OR 10 group with R 10 being either hydrogen or an optionally substituted C 1-6 aliphatic group;
or X—B with
X representing a bond, an —NH— group, a —(C═O)— group, a linear C 1-2 alkyl chain, —O—, —S— or an —SO 2 — group; preferably X represents a bond or SO 2 ; and
B representing a phenyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system selected from a heterocyclyl, preferably from:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
W represents substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 , OCF 3 , unsubstituted C 1-6 alkyl and/or unsubstituted C 1-6 -alkoxy; preferably represents H;
r represents either 0, 1, 2 or 3; preferably is 0;
with the proviso that
if in a compound according to general formula (IAb) R 2 represents a hydrogen atom;
R 4 may not represent a substituted or unsubstituted C 1-2 alkyl group; an unsubstituted benzyl group; a C 3-8 substituted alkyl group; a substituted alkyl-aryl group;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
29 . Substituted pyrrolidine compounds according to claim 1 of general formula (IB),
wherein
R 2 represents a hydrogen atom; a substituted or unsubstituted aliphatic group; a (C═O)—R 8 group; a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH;
R 3 and R 4 , equal or different, represent a hydrogen atom; an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; with the condition (proviso) that
R 3 and R 4 may not at the same time represent a hydrogen atom;
or
R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 10 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
R 6 represents a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 8 represents a hydrogen atom; a branched or unbranched, saturated or unsaturated, unsubstituted aliphatic group;
R 9 , R 10 and R 11 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 12 and R 12a , identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, Optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
30 . Substituted pyrrolidine compounds according to claim 29 ,
wherein R 2 represents a hydrogen atom; a methyl, ethyl, propyl or butyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a (C═O)—R 8 group, with R 8 representing a hydrogen atom; a methyl group; an ethyl group; a propyl group; a butyl group; a pentyl group; a hexyl group; or a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; preferably R 2 represents a hydrogen atom; a (C═O)—R 8 group, with R 8 representing a hydrogen atom; a methyl group; an ethyl group; a propyl group; a butyl group; a pentyl group; a hexyl group R 3 and R 4 , identical or different, represent a hydrogen atom; a saturated or unsaturated, unsubstituted C 3-8 aliphatic group; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group; an unsubstituted heteroaryl group; a saturated or unsaturated, optionally at least mono-substituted alkyl-cycloalkyl group; an unsubstituted alkyl-aryl group; a saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group; with the condition that R 3 and R 4 may not at the same time represent a hydrogen atom; or R 3 and R 4 together with their bridging nitrogen atom form
1) a ring system A, comprising:
and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
2) an A-X—B group,
wherein
A represents a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a linear C 1-2 alkyl chain, —O—, or a —SO 2 — group;
B represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
3) an A-X—B—Y—C group,
wherein
A represents a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 ; a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a (C═O)—OR 10 group with R 10 being a linear or branched C 1-6 alkyl group;
X represents a bond, a —NH— group, a —(C═O)— group, a linear C 1-2 alkyl chain, —O—, or a —SO 2 — group;
B represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; or a ring system comprising:
which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 alkoxy group;
Y represents a bond, a —NH— group, a linear C 1-2 -alkyl group;
C represents an aryl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group; a naphtyl group which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkoxy group;
R 6 represent an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; preferably represents an optionally at least mono-substituted aryl group;
R 8 represents a hydrogen atom; a branched or unbranched, saturated or unsaturated, unsubstituted aliphatic group;
R 9 , R 10 and R 11 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 12 and R 12a , identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system; optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof.
31 . Substituted pyrrolidine compounds according to claim 1 according to general formula (I),
wherein R 1 represents H or C(O)OCH 3 ; R 2 represents a hydrogen atom; a substituted or unsubstituted aliphatic group; a (C═O)—R 8 group; a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH; R 3 and R 4 , equal or different, represent a hydrogen atom; an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; with the condition (proviso) that R 3 and R 4 may not at the same time represent a hydrogen atom; or R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 10 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group; R 8 represents a hydrogen atom; a branched or unbranched, saturated or unsaturated, unsubstituted aliphatic group; R 9 , R 10 and R 11 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system; R 12 and R 12a , identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
32 . A process for the manufacture of substituted pyrrolidine compounds of general formula (I) according to claim 1 , characterized in that at least one pyrroline compound of general formula (II),
wherein R 1 has the meaning given above, is reacted with a per-acid, preferably MCPBA to form a compound of general formula (III),
wherein R 1 has the meaning given above, followed by reacting the epoxyo-pyrroline compound of formula III with a compound of formula (IV)
together with LiClO 4 , ACN at preferably 90° C. to give a compound of formula I, in which R 2 is H; alternatively followed by reacting the pyrrolidine compound of formula I with a base to give a compound of formula I, in which R 2 has the meaning according to claim 1 .
33 . A medicament comprising at least one substituted pyrrolidine compound of general formula (I) according to claim 1 ,
wherein
R 1 represents a hydrogen atom, an unbranched or branched, saturated, optionally at least mono-substituted C 1-6 -aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; an optionally at least mono-substituted benzhydryl group; a (C═O)—R 5 group; a group; a (SO 2 )—R 6 group; or a (C═O)—NR 7 R 7a group;
R 2 represents a hydrogen atom; a substituted or unsubstituted aliphatic group; a (C═O)—R 8 group; a benzyl group which is optionally substituted by one or more substituents independently selected from the group consisting of F, Cl, Br, I, NH 2 , SH, OH;
R 3 and R 4 , equal or different, represent a hydrogen atom; an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group in which the cycloalkyl group may be optionally at least mono-substituted; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be optionally at least mono-substituted and/or condensed with a mono- or polycyclic ring system; with the condition (proviso) that R 3 and R 4 may not at the same time represent a hydrogen atom;
or
R 3 and R 4 together with their bridging nitrogen atom form
1) a saturated or unsaturated ring system A, comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Br, I, NH 2 , SH, OH 1 CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
2) an A-X—B group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 2 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
3) an A-X—B—Y—C group,
wherein
A represents a saturated or unsaturated ring system comprising 1 to 3 optionally condensed rings, in which additionally at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
X represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
B represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
Y represents a bond, a —NH— group, a —(C═O)— group, a branched or linear, optionally substituted C 1-6 -aliphatic chain, —O—, or a —SO 2 — group;
C represents a saturated or unsaturated ring system comprising 1 to 2 optionally condensed rings, in which at least 1 carbon atom is optionally replaced by N, S or O and which is optionally at least mono-substituted by F, Cl, Br, I, NH 2 , SH, OH, oxo, CF 3 , a C 1-6 -aliphatic group; a C 1-6 -alkyl-aryl group; a C 1-6 -alkyl-heteroaryl group; a C 1-6 -alkoxy group; a (C═O)—R 9 group; a (C═O)—OR 10 group; a CH2-(C═O)—O—R 11 group; a (SO 2 )—R 11 group; a NH—R 11 group; or a (C═O)—NR 12 R 12a group;
R 5 and R 6 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 7 and R 7a , identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloalkyl group, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; an optionally at least mono-substituted aryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; an optionally at least mono-substituted heteroaryl group which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 8 represents a hydrogen atom; a branched or unbranched, saturated or unsaturated, unsubstituted aliphatic group;
R 9 , R 10 and R 11 represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono- substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
R 12 and R 12a , identical or different, represent a hydrogen atom, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing alkyl-cycloalkyl group; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-aryl group in which the aryl group may be condensed with a mono- or polycyclic ring system; a branched or unbranched, saturated or unsaturated, optionally at least mono-substituted alkyl-heteroaryl group in which the heteroaryl group may be condensed with a mono- or polycyclic ring system;
with the provisos that
if R 2 represents a hydrogen atom;
and R 1 represents a hydrogen atom or a condensed aryl group;
R 3 and R 4 may not form together with their bridging nitrogen atom a triazole group;
if R 2 represents a hydrogen atom;
and R 1 represents a hydrogen atom; a substituted C 1-2 alkyl group; a condensed aryl group; a benzyl group;
R 3 and R 4 may not form together with their bridging nitrogen atom a substituted, unsaturated, condensed ring system containing at least 4 nitrogen atoms as ring members; an unsaturated, (C═O)-substituted, uncondensed, 6-membered ring system in which two carbon atoms are replaced by nitrogen.
if R 2 represents a hydrogen atom;
and R 3 and R 4 form together with their bridging nitrogen atom a pyrrolidine ring, a piperidine ring, a piperazine ring or a morpholine ring;
R 1 may not represent a hydrogen atom; a methyl group; an unsaturated tert-butyl group; a (C═O)-substituted alkyl-heteroaryl group;
if R 2 represents a hydrogen atom;
and R 1 does not represent a benzyl group;
and either R 3 or R 4 represents a hydrogen atom;
either R 3 or R 4 may not represent a substituted alkyl-heteroaryl group; an alkyl-aryl group; a substituted heteroaryl group; an unsubstituted methyl group; a substituted alkyl group; an aryl group; a cyclohexyl group; an alkyl-cycloalkyl group wherein the cycloalkyl group contain at least one heteroatom;
if R 2 represents a hydrogen atom;
and R 1 represents an alkyl group;
and either R 3 or R 4 represents a hydrogen atom;
either R 3 or R 4 may not represent a substituted or unsubstituted C 1-2 alkyl group; a branched C 1 - 1 alkyl group; a substituted or unsubstituted C 3-6 cycloalkyl group in which optionally at least one carbon atom is optionally replaced by N, S or O; a cycloheptyl group;
if R 2 represents a hydrogen atom;
and R 1 represents an alkyl group;
either R 3 or R 4 may not represent a cyclohexyl group while the other represents at the same time an alkyl-aryl group; or either R 3 or R 4 may not represent an alkyl group while the other represents at the same time an alkyl-aryl group;
if R 2 represents a hydrogen atom;
and R 1 represents a benzhydryl group;
and either R 3 or R 4 represents a hydrogen atom;
either R 3 or R 4 may not represent a (C═O)-substituted alkyl-aryl group; a (C═O)-substituted aryl group;
if R 2 represents a hydrogen atom;
and R 1 represents benzyl;
and either R 3 or R 4 represents a hydrogen atom;
either R 3 or R 4 may not represent a substituted or unsubstituted C 1-2 alkyl group; a substituted C 3-8 alkyl group; a substituted aryl group; a substituted alkyl-aryl group;
or
R 3 or R 4 , together with their bridging nitrogen atom may not form a tetrahydropyrimidine ring; a triazolo pyrimidine ring;
if R 2 represents a benzyl group;
and either R 3 or R 4 represents a hydrogen atom;
either R 3 or R 4 may not represent a (C═O)-substituted alkyl-aryl group;
if R 2 represents a C 1-3 alkyl group;
and either R 3 or R 4 represents a hydrogen atom either R 3 or R 4 may not represent an unsubstituted C 1-2 alkyl group; a substituted alkyl group; a substituted or unsubstituted aryl group; a substituted heteroaryl group; a (C═O)-substituted alkyl-aryl group;
optionally in form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in form of a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a corresponding salt thereof, or a corresponding solvate thereof, or a prodrug thereof,
and one or more pharmaceutically acceptable excipients and/or carriers.
34 - 57 . (canceled)
58 . A method for the prophylaxis and/or treatment of a sigma receptor-mediated disease or condition, which comprises administering to a subject in need thereof at least one substituted pyrrolidine compound according to claim 1 .
59 - 63 . (canceled)Join the waitlist — get patent alerts
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